


Meet The Parents

by assbuttintheimpala



Category: Supernatural
Genre: Age Difference, Alternate Universe - High School, Alternate Universe - Human, Anal Sex, Blow Jobs, Bondage, Bottom Castiel, Butt Plugs, Come play, Crossdressing, Dirty Talk, Felching, Hand Jobs, M/M, Older Dean, Panty Kink, Riding, Rimming, Top Dean, Younger Castiel, face riding
Language: English
Status: Completed
Published: 2013-12-08
Updated: 2013-12-16
Packaged: 2018-01-04 02:39:07
Rating: Explicit
Warnings: Underage
Chapters: 2
Words: 10,530
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1075550
Author URL: https://archiveofourown.org/users/assbuttintheimpala/pseuds/assbuttintheimpala
Summary: <blockquote class="userstuff">
              <p>After three months of being together Dean is finally going to meet Castiel's parents</p>
            </blockquote>





	1. Chapter 1

**Author's Note:**

> I have two parts to this and I was going to post it all together but the second part is taking forever for me to write so I thought I'd post the first and you guys can motivate me to write the second faster

"You can do this. You are Dean Winchester. There is no way that you are going to screw this up." The words reflected back to him in his bathroom mirror as he adjusted the tie to his suit. He was dressed in a white button down with a black and white striped tie and black slacks. His suit jacket was sitting on the back of his desk chair in his room which he would put on just as he was leaving so he didn't wrinkle it. He definitely didn't want any wrinkles tonight. It was an important night and he _did not_ want to screw it up.

With one final glance in the mirror and one more hand to his hair to flatten his comb over, he let out a sigh and headed to his room where he sat on the end of his bed. He bent down to put on his black leather shoes which he had just polished so they were shiny and clean before he reached over and grabbed his phone.

_Leaving now. Be there soon. xox_

He clicked send after typing the number he had learnt off by heart after five minutes of having it because even back then he knew it was a number he needed to remember. When the reply came in with a 'See you soon' and a smiley emoticon, Dean couldn't help but smile and feel some of the nerves that had been churning in his gut ever since he had been asked to do this, dissipate.

Castiel Novak was his boyfriend of three months and tonight was the night he was going to be introduced to his parents. According to Cas, they didn't care that their son was gay all they cared about was that the boy their precious son settled with was the right one for him. He knew, from what Cas had told him of his parents, that they had very high expectations for their son and that spanned over all aspects of his life including who he chose to date. The Novaks were proud people who were very well off and were rather selective with whom they chose to socialise with. There were times when Dean and Cas were alone that Cas would confess to not liking how his parents acted but he still loved them all the same. Dean knew he needed to make the right impression and by dressing in the suit he wore to his Uncle Bobby's wedding when he finally got his act together and married Ellen Harvelle, it was the first step to giving that impression.

The teen pocketed his phone making sure to put it on silent so that if it did go off during dinner he wouldn't seem like a rude teenager who couldn't be away from his phone for one measly dinner. He knew it more than likely wouldn't go off seeing as the only people that messaged him was Cas and his little brother, Sam. Sam knew all about the importance of the dinner and knew better than to text his brother but it was better to be safe than sorry. Once he had slipped his jacket onto his shoulders, Dean smoothed his hands down the front as he buttoned the top button and let out another breath before grabbing his wallet and trotted down the stairs. When he got there, he was greeted by his mother, Mary, who was beaming at him.

"You look so handsome. There's no way they aren't going to like you" she gushed. When he reached the bottom, she reached out and pulled him into a hug and whispered into his ear. "Stop worrying. Anyone with eyes can see how smitten you two are for each other. They won't do anything to jeopardise that" Dean nodded as he inhaled his mother's scent which never failed to calm him. She pressed a kiss to his cleanly shaved cheek which he knew Cas would hate but he didn't think his parents would appreciate the three day stubble he usually displayed. With a smile she pulled away from him and tapped his cheek lightly with her soft finger tips "Off you go. You don't want to be late".

"Yeah" Dean replied dumbly "I'll see you later" Dean kissed her cheek and gathered the keys to his Impala which had come into his possession almost two years ago on his sixteenth birthday and he had acquired his driving license. His father, John, had given it to him and told him to look after the vehicle which he did even if he did have to put in a lot of elbow grease to get rid of the stains he and Cas left in the back seat on a number of occasions. It was worth the sore arm any day to see Cas writhing and pleading for Dean as he hovered over the top of him teasing and giving him everything but what he wanted. But tonight, not even those thoughts could calm his nerves because he knew if he screwed things up with Cas' parents then he and Cas' relationship could cease to exist. But he couldn't think about that right now. All he had to do was do the best he could and hope for the best.

Dean started his Impala with a roar and relished the somewhat calming rumble of his vehicle. As he drove, he thought over what he would say and topics he would avoid. Particularly the ones that weren't ones you would share to anyone especially your boyfriend's parents and unfortunately how they met fell into that category.

It was at a Halloween party that they first met three months earlier which Cas' parents didn't even know Cas attended. He was supposed to be studying with his friend Anna but had snuck out to attend the party. Dean wasn't initially going to go but had reluctantly agreed when his friend Jo has begged him to go with her. He hadn't dressed up extravagantly instead choosing to grab a Zorro mask and a black cape as a last minute costume while he dressed in black jeans that were a little tighter than his usual attire and a black tee that hugged his figure well. Dean knew he was hot and there was no harm in showing it off.

When they arrived at the party, Dean found himself ditched. Jo had run off with a friend of hers leaving Dean by himself stood in the doorway in a sea of unfamiliar faces. Jo was a childhood friend but they attended different schools meaning not all Jo’s friends were Dean’s friends. Jo attended private school while Dean was in the public system. It meant that when Jo dragged him to rich-boy parties such as that one, he often found himself looking for someone to hook up with because Jo more often than not left him to socialise. That night though as Dean scanned the crowd he didn't find anyone that caught his eye. Of course it was still early so with a sigh Dean headed for the kitchen to find a drink. When he got there he was greeted to the sight of a fantastic ass clothed in a tight white mini skirt. As Dean moved closer, he realised the owner of the fantastic ass was dressed as a nurse and was in fact a very handsome guy. Dean had been open about his sexuality for a while and there was no way he was going to pass up the opportunity before him.

Once he was close enough, Dean grabbed a red solo cup and filled it with the liquid from the keg before turning his sights to the nurse. The guy was absolutely gorgeous and Dean's breath caught in his throat as he took in the teen's appearance. He had startling blue eyes that were a contrast to his almost black hair that was artfully messed beneath a nurse hat and the bright red lipstick spread over his gorgeous lips. He was about the same height as Dean but Dean was slightly taller and given by the soft features of the other teen, a little older. Dean's eyes raked over the teens form taking in the tight white blouse with a red trim that was unbuttoned to show a teasing amount of chest before moving lower to take in the long smooth legs that had obviously been shaved for the occasion before finishing at the black pumps that accounted for his height. It was obvious by the way the teen was stood that he was confident in his outfit but as Dean's eyes trailed back up to the teen's face, he smirked as he saw the scarlet blush that had filled his cheeks as he noticed Dean's stare. With the window open, Dean made his move.

"Hey I'm Dean" he greeted with his winning smile that never failed to get him laid.

"C-Castiel" the other boy stuttered and Dean couldn't find it utterly adorable.

"Well Cas, let me get you a drink" just as Dean went to move to get another cup, Cas spoke.

"Thank you but I don't drink" the boy said timidly.

"Oh come on. You're at a party. Surely one drink couldn't hurt?" Dean knew it was peer-pressure and he normally wasn't one that pressured people into doing something they didn't want to but the guy looked as if he was wound so tight and needed to let loose a little. The younger teen bit down on his lower lip chewing on it in deliberation before relenting and giving Dean a shy smile and nodded. As one drink turned into two and two turned into three, Dean discovered why Cas would rather not drink. The teen turned into a clingy, touchy drunk not that Dean minded one iota because it was him who Cas decided to hang off.

They sat on a couch in the living area which was filled with dancing bodies with Cas pressed into Dean's side as close as physically possible with Dean’s arm draped over his shoulder Cas’ hat nowhere in sight. He was whispering random facts about bees into Dean's ear and Dean couldn't help but laugh at how cute it was. It was strangely endearing and Dean found himself hooked to the strange teen. They had chatted over their drinks getting to know each other more and as they did, Dean found himself being drawn in by the teen's strangeness and unique approach to things. Dean had assumed correct in thinking the boy was younger and found out that he was a sophomore at Jo's school whereas Dean and Jo were both seniors. The night moved onward as Cas downed the rest of his drink marking his fourth of the night. With it Cas' forwardness increased and Dean's free hand that wasn’t wrapped around Cas was taken by Cas' and placed onto the younger boy's inner thigh. Dean inwardly groaned at the smoothness under his fingertips as Cas slid his hand higher and underneath the hem of the mini skirt. Cas' hand stopped moving Dean's and Dean didn't dare move it any higher.

"Can I tell you a secret?" Cas whispered into his ear.

"Mmm? And what's that baby?" Dean hummed in reply which earned a giggle from the teen. Before Dean's alcohol clouded mind could register what was happening, Cas moved to straddle Dean's lap his knees pressed either side of Dean's hips with his hands on his shoulders. Dean's body reacted faster than his brain and moved his hands to grip Cas' hips.

The younger teen moved in so his breath was ghosting over the shell of Dean's ear causing a shiver to pass down his spine. "I'm wearing panties" he breathed before he gripped Dean's hand and slid it up his thigh so his fingers pressed against silk fabric. Dean let out a small groan when he felt them while Cas let out a small sigh while pressing Dean's hand further up his leg so Dean's fingers were pressed up against his crotch. "I want you to bend me over and fuck me in them" Cas demanded into Dean's ear.

Dean didn't waste a second. He moved his hand from Cas' hip and placed it into the brown locks where he pulled tight which forced Cas' head back so Dean could look him in the eye. As soon as he could see him, he leant in and placed his lips onto the other teen's. When Dean licked along Cas' lips he couldn't help but groan as the other teen opened up so willingly for him to enter his mouth. His tongue plunged inside mapping out every nook and cranny and the spots that made Cas' hips buck into Dean's. As Dean’s tongue explored, Cas’ hips continued to rock into Dean’s until the friction was too much and not enough at the same time. Dean yanked on Cas’ hair pulling the teen away from him and smirked at the whine the nurse let out.

“How ‘bout we find somewhere a little more private?” Dean purred into Cas’ ear who quickly nodded before gracefully sliding off Dean’s lap and stood to his feet. Their twin erections were glaringly obvious along with the red lipstick that was no doubt smudged across Dean’s lips as they walked towards the back of the house where the bedrooms were located. Cas led the way as he had told Dean earlier that the person throwing the party was a close friend of his so he knew where to go. Dean didn’t mind one bit as he followed Cas through the house unashamed to be openly staring at Cas’ ass. Once or twice Cas had turned around and caught him staring only to blush a deep red and turn back to look where they were walking. No one bothered them as they walked and soon enough they were stepping into a dark bedroom with a double bed in the middle. “Whose room is this?” Dean asked not really caring for the answer but curious all the same.

“My friend’s, Gabriel” Cas replied with a smirk while he shut the door and moved towards Dean confidently even while still wearing the black heels. “He’s a bit of an ass at the best of times.” Dean let out a chuckle at that and saw that it had Cas smiling at him.

“Well then, let’s deface his bed” Dean said with a grin before cupping Cas’ cheek and guiding their mouths together. Cas moaned into the kiss as his hands cupped Dean’s cheeks. Cas moved away prematurely and Dean frowned in confusion before his hands came up to remove the mask that was over his face and threw it aside. With the mask removed, Dean leant forward again and pressed their lips together again already addicted to the taste of Cas. As their tongues tangled, Dean walked them backwards towards the bed where he sat down and pulled Cas into his lap just like they had on the couch. His hands rubbed up the smooth texture of Cas’ thighs and stroked teasingly over the fabric of his panties.

When the need to breathe became a necessity, Cas pulled away and slipped off Dean’s lap where he parted Dean’s legs so he could nestle between them. Nervous hands fumbled with the zipper and Dean ran his hands through Cas’ hair in a soothing gesture to calm the teen. Dean hissed when a warm hand wrapped around his dick and pulled him out into the cool air but any thought other than Cas was pushed from his mind as the teen looked up at him through his lashes as he wrapped his smudged lipstick clad lips around his cock.

“Fuck” Dean groaned as Cas’ tongue swirled around the head his fingers clenching tightly into the locks beneath them. His cheeks hollowed as he sucked and glided his lips lower taking more of Dean into his mouth. “Jesus” he panted as Cas continued to slide until his nose was pressed into the brown curls at the base. Cas never moved his eyes away from Dean’s as he sucked so eagerly on the dick in his mouth and Dean found he couldn’t look away caught in a trance of pleasure. Cas pulled back up to the head and rolled his tongue over the slit lapping at the pre-cum before swiping along the bundle of nerves under the head. Dean’s eyes nearly rolled back into his head as Cas worked on trying to suck him off but Dean wasn’t going to give him the pleasure of tasting him. Not yet anyway.

He pulled harshly on the hand that was locked around the brown hair yanking Cas off his dick with a wet pop. The needy whine Cas let out had another pearl of pre-cum drip from the tip. Cas eyed it with wide eyes as he licked his lips. Dean followed his line of sight and smirked before moving his free hand to swipe a finger over the drop and reached it towards Cas’ mouth. The teen eagerly grabbed on and sucked on Dean’s finger. Dean pulled back after a moment before slipping two fingers inside which Cas easily swallowed around his tongue working over the digits just like they had to his cock just minutes ago.

“That’s enough” Dean growled and Cas obediently let the fingers slip from his mouth which had Dean letting out a small groan “Fuck you’re so obedient aren’t you baby” Dean praised before he pulled at Cas and settled him in his lap once again. They kissed some more Dean savouring the taste of himself on Cas’ tongue before he pulled away and turned them so Cas was settled on his back. Dean buried his face into Cas’ neck biting and licking his way down the expanse of skin. Cas was letting out needy little whines as his hips bucked up into Dean while he worked. “Needy little thing aren’t you?” Dean teased while he worked on the buttons of the tight white blouse. Cas’ chest was heaving as Dean worked staring down at the newly revealed skin with hungry eyes. He wanted nothing more than to taste and mark every inch of skin that he could but it would have to wait for another time because he was unbelievably turned on and there was no way he could wait much longer.

With the buttons undone, Dean lifted Cas up to remove it from his shoulders before he undid the button of the skirt and slipped it down Cas’ legs to reveal the black silk panties that were straining to keep him held inside. He threw the skirt in the general direction he did the shirt while his hands gently slipped the heels from Cas’ feet and let them fall to the floor with a thud but his eyes were still firmly locked on the black panties. There was a large damp spot in the front from where he had started to leak through and Dean couldn’t help himself as he leant down to suck at the spot. A cry of Dean’s name filled the room as he mouthed at Cas’ cock through the fabric which had Dean grinning before pulling back.

“Hands and knees” he demanded and Cas scrambled to comply positioning himself as Dean had instructed with his head buried in the pillows. He was shaking where he sat with need and Dean pitied him slightly. “So fucking gorgeous you know that?” he praised as he worked on the tie of his cape and let it fall to the floor. Next to go was the shirt followed by his jeans and boxers. He searched for his wallet in the back pocket of his jeans and removed the small packet of lube and the condom he always kept in there for situations exactly like this one. He threw them on the bed close to Cas who looked down at them and visibly shivered in anticipation. Dean slid onto the bed on his knees and inched closer to Cas where he positioned himself between his spread knees.

When his hands pressed against the teen’s back, Cas pressed back into the touch a silent plea for more. Dean was more than happy to move things along and slowly slid his hands down to the waistband of the panties. He pulled them down and over the globes of his ass and nestled them below his sac. Cas gasped at the touch but didn’t utter another sound as Dean grabbed hold of the lube. He ripped open the packet and squirted half of the liquid onto his fingers where he rubbed them together to warm them up. Once satisfied, he pushed at Cas’ knees with his dry hand in indication to spread them wider. Cas did so which exposed the pink rim of his hole which looked virgin tight. Unable to control himself much longer, Dean raised his dry hand to Cas’ hip while his lube slick fingers traced over the rim. Cas groaned and pushed back against the touch.

“Please” he whined while Dean continued to tease. “Dean, please” he said again when Dean made no move to enter him.

“Such a needy little slut aren’t you Cas” he teased while he watched his fingers as they played with the tight muscle before he slipped the first finger in easily watching as Cas’ body sucked him in eagerly. Cas’ head hung low as Dean’s finger worked inside him and his hips tried to fuck back onto the digit only to be held in place by Dean’s hand. Castiel let out a grunt of frustration as he resigned to the fact that he had to stay still which had a low chuckle escaping from Dean.

“More” Cas demanded and Dean was well over teasing now. He slipped another digit in and was surprised by the lack of resistance to his digits. His fingers slid in and out easily without much complaint from the teen below him instead he was groaning into the pillow below his face and his fingers were clenched into the sheets.

“You finger yourself before you came baby?” Dean asked as he slid in another finger. Cas nodded and let out a little whine as Dean spread his fingers wider “Expecting to get lucky huh Cas? Bet you were picturing a fat cock in your ass as you did it. Dressed up like a slutty little nurse just begging to be fucked aren’t you?”

“Yes!” Cas keened “Please Dean. Fuck me. Want it so bad”

“I know you do baby” Dean taunted as he pressed his fingers against the bundle of nerves he had been purposely avoiding. He watched as Cas bowed into the touch and let out a high pitched yelp at the sensation. His muscles clenched around Dean’s fingers and Dean couldn’t stop the groan that was let out as he imagined his dick being inside the heat. Dean pulled his fingers free watching as Cas clenched absently around the emptiness while he blindly reached for the condom. He tore open the package and rolled it on before retrieving the half empty packet of lube and smothering it on his dick. He couldn’t help but groan at the pressure as he stroked himself taking the edge off slightly after having ignored it for so long. Satisfied he was slick enough, Dean placed both his hands onto Cas’ hips and lined up with his stretched entrance. Dean didn’t even have to wait before Cas was sliding back onto him with such a force that he was sure it was going to hurt him but the high pitched moan that he let out told him otherwise.

Dean’s balls slapped against Cas’ ass as he bottomed out and he had to grip tighter onto Cas’ hips to stop him from moving. Sure Cas seemed to be okay but Dean was so close to the edge he just needed a minute or it was going to be over way too soon.

“Dean” Cas whined “Dean move”

“Hold on baby” Dean panted “I need a minute” Cas obliged although he started to clench his muscles around Dean and Dean growled at the motion which earned him a small smirk from Cas over his shoulder. “Little shit” Dean snarled before he pulled out and slammed back in which had Cas keening into the air.

“Fuck” Cas gasped as Dean repeated the motion over and over pulling Cas’ hips back onto him as he thrust forward. Needy little pants of air fell from Cas’ lips as they moved together along with a string of curses and Dean’s name. “Fuck… harder Dean” Cas pleaded his fingers clenching even harder into the sheets causing them to bunch under his palms. Dean snarled as he picked up the pace before he pushed Cas’ head down into the mattress to change the angle and give himself more leverage. Dean pushed himself to his feet slightly so he could slam into Cas even harder. Cas had turned his head to the side so Dean could still hear the breaths being punched out and the gasps to catch it again. “Oh god Dean” Cas panted as he writhed and clenched down hard on Dean’s cock.

“Just can’t get enough can you Cas? Such a greedy little slut bet I could just stop right now and you’d keep fucking yourself to get more” Dean grunted as he continued to pound into the tight heat his hand still pushing Cas’ head into the mattress. He knew by the way Cas was groaning and clenching that he was close and Dean wasn’t doing much better himself. It was going to be over soon but he was going to make sure Cas got there first. Dean repositioned to his knees and draped himself over Cas’ back his hips continued to rock as he reached around and slid his hand into the silky panties where he pushed them down to Cas’ thighs before he fisted Cas’ hard cock. Cas groaned as Dean took hold and started to strip him in a tight fist. Cas’ hips were rocking back and forth between Dean’s cock and his fist. “Come on Cas. Fuck yourself on my dick. Get yourself off and cover yourself in cum. Do it baby” Dean whispered into Cas’ ear before he moved to suck on his neck leaving a bright red mark which he soothed with his tongue while Cas’ hips continued to move doing exactly what Dean had asked. “Mmm just like that baby” Dean cooed into Cas’ ear.

Dean felt the urge to come build higher and higher in his gut until he couldn’t take the pace much longer and started to slam his hips harder into Cas. Cas moaned in approval and Dean just pumped harder. They moved in tandem with Cas still fucking his hips back onto Dean’s cock when Dean pulled back and his hand still stripping Cas’ cock but the pace was erratic and electric sending pulses of pleasure through Dean until final Cas gasped out his name and came all over his hand and over the sheets below him. The pressure around his dick had him crying out Castiel’s name while his hips stuttered and he came into the condom.

Panting, they both came down from their highs as Dean pulled out and collapsed to the side while Cas slumped down and stayed lying on his stomach. After Dean had caught his breath, he looked to the side to see Cas smiling shyly at him. Dean eagerly returned the smile before he raised his arm closest to Cas and reached over to pull the other teen towards him. Cas came willingly and snuggled into Dean’s side with his head rested over Dean’s heart.

“I gotta ask man,” Dean said breaking the post-sex haze “Why a nurse?”

It was then the story came out that Cas’ parents thought he was studying at Anna’s house and how Anna had organised their costumes. Cas had a thing for cross-dressing and everyone knew as much so it wasn’t a big deal for him to show up at a party wearing a skirt and heels. When Cas confessed that Anna had only provided the skirt and blouse the rest was from his own wardrobe, Dean’s thoughts went to a dangerous place where he thought of what _else_ Cas had in that wardrobe. It was dangerous territory at the time as Dean had never been in a committed relationship and he didn’t even know if Cas wanted more than what they had that night. So to test the waters, Dean decided to subtly hint at wanting to see Cas again.

“Maybe you’ll have to show me the rest of that wardrobe of yours?” he asked while he stared at the ceiling. The hand that had been tracing over his abdomen stopped and Dean felt the pressure of Cas’ palm before the teen was rising up to look at Dean.

“You want there to be more than this?” Cas asked with his head tilted adorably to the side and Dean almost melted on the spot at the hope that glistened in his eyes.

“Yeah” Dean said his throat tight “Yes I do” he said again after clearing his throat. Cas had attacked him with kisses then leaving a hickey of his own into Dean’s neck low enough for him to hide and another just below his ear which would be a lot harder to cover up.

After some more hefty making out, they were rudely interrupted by a cellphone ringing. Cas groaned into the skin he was working over on Dean’s neck before he pushed himself up and fixed his panties back into place before he slunk off the bed to ransack through his clothes before he found his phone. He pulled it out and grimaced at the screen before answering it. It had been his mother asking him to come home and Cas had said he would be home soon they just had a few things they still needed to do for their assignment but he would text them when he left. Dean had tried to hide the hurt but apparently he wasn’t very good. Cas had moved back to straddle him and placed a heated kiss to his lips which had promised more before he pulled back again and slowly started getting dressed. Dean watched idly from the bed as the skin he had been touching and licking was slowly covered up once again. He was confused for a moment when Cas searched through the drawers next to the bed but when he pulled out a pen and grabbed Dean’s arm, he knew what he was doing. Cas wrote down his number onto Dean’s skin and when he was done, Dean stared at the numbers and committed it to memory.

The next morning, Dean had called Cas and the rest was history. They would meet up after school with Dean picking Cas up after his various after-school commitments and they’d spend the evening together driving around in the impala and finding a secluded spot where they could do what they like. Of course not every time they met they would have sex as there were times when they would just go to a diner and talk over a meal. It was peaceful and it was perfect. Eventually, after two weeks of them being an item, Dean dragged Cas home to meet his family who welcomed him with open arms. His parents were accepting and didn’t bat an eye at Cas the first time he decided he wanted to wear lipstick while he was over. But now it was Dean’s turn to meet Cas’ parents. They had put it off for so long because Cas was worried his parents wouldn’t be accepting of Dean. His parents knew that Cas was seeing someone and had told Cas that they would like to meet him a month into their relationship but Cas had put it off saying it wasn’t very serious even though that was far from the truth seeing they had talked about a future together. However, now that they were three months in, Dean had finally talked Cas around into meeting his folks. It was how Dean found himself driving over to his boyfriend’s house nervous as hell that everything was going to crumble around them and Cas would be forced to leave him and not even the thoughts of their first night together was calming the pit of worry in his gut.


	2. Chapter 2

**Notes for the Chapter:**

> I'm so sorry for taking so long. It's a few days late but it's here and I hope you like it. I have updated the tags so please check them before venturing forward :) Thanks for your patience

Castiel took a final glance in the mirror and tried to tame his messy hair he was plagued with but it failed to comply. He knew his boyfriend loved it that way telling him it made him look like he’d just been thoroughly fucked but tonight was important and he wanted his parents to like Dean. They had such high expectations for everything he did including who he dated even though it didn’t concern them at all. Everything he did as he grew up he did to please them. He was forced to join almost every after-school club there was and to push himself to get the best grades he could. If he got anything below a B, it was seen as a failure in his parents’ eyes. But once he started high school, he started to curve off the straight and narrow and take a few detours along the way. He started to give in when his friends begged him to go to parties instead of staying home and studying as well as lying to his parents of his whereabouts. It was because of his new attitude towards his life that he met Dean. Of course when the time came he told a partial lie and just told his parents he met Dean at a study group at Gabriel’s and that even though they went to different schools they were studying a similar topic. His parents had gobbled up the lie and gave a curt nod at the fact that Dean seemed to be just as academically focussed as Castiel. What his parents didn’t know was that Dean was actually in his final year of school making him two years older than Castiel and he knew it was going to come out tonight, he just hoped his parents wouldn’t be too upset about it.

To be honest, however, Castiel didn’t care what his parents thought of Dean. All he knew was that he was in love with Dean and he was pretty sure that Dean was in love with him which was all that mattered. His parents had controlled his every move up until he was 14 and started high school and he now knew that even if they didn’t approve, he wasn’t going to let them ruin the best thing that had ever happened to him.

With his appearance as good as it was going to get, Castiel left the bathroom and headed downstairs. Dean had messaged him just prior to leaving so he knew he wouldn’t be too far away as they only lived a short drive away from one another. He was desperate to reach the door before his parents so that he could greet Dean and probably calm the nerves of the older boy. He knew that Dean would be freaking out about the whole meet the parents because of what Castiel had told him about said parents. When Castiel had gone to meet Dean’s parents, he had been slightly nervous but upon meeting them he had calmed down as he saw how genuine and accepting they were. It didn’t take him long to become comfortable to be himself around them and was soon wearing make-up while he was in their presence. The lack of judgement was refreshing and he really, really loved being a part of Dean’s family. He just wished that his parents would react the same way to Dean.

Silently, Castiel made his way downstairs wearing his black dress slacks and a white button down minus the tie that he would normally don for formal occasions but just didn’t feel the need to wear one so instead he just left the top couple of buttons undone and sat on the bottom step waiting for Dean to turn up. He fiddled with his phone as he waited with his knee jumping up and down in nervous anticipation. Knowing Dean wouldn’t ring the doorbell and would instead message him when he got there, he kept his phone in hand waiting for the text to come through. Minutes passed and finally Castiel’s phone vibrated to life with a message from Dean saying ‘I’m here’. Castiel rushed to his feet and fled to the door opening it and stepping outside firmly closing it behind him so he could get a moment alone with Dean.

Without a word uttered, Castiel flung himself into Dean’s arms and wrapped his hands in Dean’s hair moulding their mouths together in a heated kiss. Once satisfied, he pulled back taking in Dean’s features as he went. He grimaced as he realised Dean had shaved the stubble that he loved so very much. He didn’t know why but having the feel of the unshaven cheek brush against his skin – even in the raunchier of places – turned Castiel on to no end. When he flexed his fingers in Dean’s hair, he became aware of the gel that was in it and the disgusting comb-over Dean had styled his hair in. Without explanation, Castiel moved his fingers through Dean’s hair and ruffled it into its normal state.

“You’re trying too hard” Castiel smiled as he pressed a chaste kiss to Dean’s pout at having his appearance altered. “You need to relax and be yourself not what you think they want you to be”

“I just want them to like me” Dean grumbled as he fiddled with the buttons on his suit jacket.

“And they will” Castiel assured as he grabbed Dean’s hands and interlocked their fingers “and if they don’t… well let’s just say I really don’t give a shit” Castiel smiled which was returned by Dean which even if it was still only small it was still enough to show that the nerves were dissipating from Dean. It was weird to see his strong, open-minded boyfriend look so nervous and bashful but Castiel found it rather endearing how much of an effort he was putting in to this dinner. He’d even dressed up in a suit, gelled his hair, and shaved for the occasion and he looked absolutely gorgeous as Castiel eyed him up and down. In response, Castiel leaned forward and captured Dean’s mouth once again with their hands still interlocked. Breathless, they parted and Castiel had a wicked thought come to mind. He leant forward and pressed his mouth to the shell of Dean’s ear and pressed a chaste kiss to the skin before he spoke. “Remember how I told you about the rest of my wardrobe? Maybe after dinner I’ll let you see some of it” he smirked as he heard Dean’s sharp intake of breath. He pulled back and pressed a kiss to Dean’s cheek smiling as he took in the pink flush that had graced his skin before he let one of Dean’s hands drop from his own so he could turn and open the door. They stepped inside the house and Dean closed the door behind him before he removed his coat and handed it to Castiel who hung it on the hook beside the door.

Wordlessly, Castiel led Dean through the house to the living room where his parents were sitting. They both had novels in hand and were reading them when they walked into the room. Castiel cleared his throat catching the attention of both his parents. They put down their books and stood to their feet before they made their way over to where the couple was stood.

“Mom, Dad, this is my boyfriend, Dean” Castiel announced nervously before he bit down on his lower lip as he waited for their reaction. The pair eyed Dean up where he stood but Dean seemed to come into his own as the situation unfolded. He stepped forward with his hand outstretched towards Castiel’s father and gave him his winning smile that had won Castiel over in an instant.

“Dean Winchester. It’s a pleasure to meet you sir” He greeted and Castiel was surprised to see his father raise his own hand and shake Dean’s with a small barely there smile on his face. “And you ma’am” Dean said as he turned towards his mother with the same smile. Castiel saw the small red tint that graced his mother’s cheeks as Dean looked at her and Castiel knew this was the best start to the evening that he could have hoped of. Apparently when under pressure, Dean thrived and was quick on his feet.

“It’s great to finally meet you Dean” his father said as he wrapped a hand around his wife’s waist “Our Castiel here has been very hush hush about you” Dean turned to Castiel then with a raised eyebrow to which Castiel just shrugged and portrayed his ‘ _I already told you that_ ’ face as Dean turned back to his parents with a smile.

“Well,” his mother began “Why don’t we relocate to the dining room and chat for a bit. Dinner shouldn’t be too far away” At that, his parents turned away from the couple and started their way towards to the dining room. Dean glanced at Castiel with a nervous smile to which Castiel just pulled him forward and pressed a kiss to his lips.

“You’re doing great” Castiel whispered before he led the way with Dean’s hand still firmly in his own.

The couple sat down at the table next to one another with Castiel opposite his mother and Dean opposite his father. It was quiet and awkward as they sat down with no one breaking the silence until finally, his father spoke asking questions about Dean’s parents and his life at home. Dean was quick to answer all the probing questions informing them about how his father was working as a mechanic at an auto-shop he co-owned with his friend Bobby, and his mother was a stay at home mother who looked after him and his little brother Sam. His parents for the most part of it weren’t condescending and would just nod along with what Dean was saying. Castiel would mention how nice his family was and how welcoming they had been when he had met them.

When their meals were placed in front of them, the topic turned more towards school. Castiel had to bite down on his lip to stop the laughter that tried to escape at the look on his parents’ faces when they learned Dean was in his final year of school. When Dean looked to Castiel with a worried glance as if he had done something wrong, Castiel just reached over and placed his hand to Dean’s thigh. He rubbed the firm muscle with a reassuring hand and Dean seemed to relax slightly under the motion to which Castiel smiled before returning his attention to his parents without removing his hand. Content with the conversation lulled for the time being, everyone ate in silence while Castiel’s hand became a little more adventurous. His hand moved a little higher on Dean’s thigh dangerously close to his groin. Castiel revelled in the shallowness of Dean’s breathing and the stiffness that took over his body as his hand moved to cup Dean’s groin. Dean coughed to cover the squeak he was about to let out as Castiel’s fingers massaged the growing bulge to stop the curious looks from Castiel’s parents. All the while, Castiel kept his face stoic as if intent on what he was eating before Dean’s flustered state became quite obvious.

“Dean?” Castiel questioned “Are you okay? You look quite flushed” When Dean turned and glared at him, Castiel struggled to keep his expression concerned. “Why don’t you go lie down for a bit? My room is upstairs second door on the right” he said with a wink which was concealed from his parents easily.

“No” Dean croaked “I’m fine” he said through gritted teeth. Castiel only smiled in reply before returning to his meal his hand still cupping Dean’s groin. His parents were oblivious to the goings on and instead continued to probe into Dean’s life. It seemed as though his parents were quite accepting of their relationship and weren’t planning on asking Castiel to end it. With that in mind, Castiel smiled as he finished his dinner with one hand the other working Dean’s groin to the point that Dean’s hips were moving forward into his hand and he was squirming in his seat. Angry glares were sent Castiel’s way but he ignored them all in favour of having the thrill of giving his boyfriend a handjob under the table in the presence of his parents. When he knew Dean was biting back groans and close to not being able to keep himself from crying out much longer, Castiel pulled back seeing that both he and Dean were done with his parents not far from finished with their meals..

“May we be excused?” Castiel asked his parents once they had both finished their meals.

“Of course, Castiel” his mother replied with a smile which Castiel returned before he stood from the table. Dean glanced up at Castiel with a ‘are you really doing this to me’ look before letting out a sigh and pushing himself up. The table was high enough to hide his bulge when he was stood and he quickly thanked Castiel’s parents for the meal before turning towards the stairs and following Castiel up them.

Once they were safely in his room with the door firmly closed behind them, Castiel found himself pinned to the wooden door forcefully with Dean pinning his wrists above his head and his legs pinning his hips to the panel.

“What the fuck was that?” Dean growled out as Castiel got over the shock of the strength behind Dean’s movement.

“Just having a little fun” Castiel smirked in reply

Dean’s eyebrows shot up and his eyes went wide before his gaze narrowed on Castiel once again. “Just having a little fun? So giving me a handjob under the table _in front of your parents_ is your idea of a little fun?”

Castiel nodded “Yep” he replied popping the ‘p’.

“Fuck you’re an asshole” Dean breathed before his lips were pressing against Castiel’s own and his tongue entering his mouth as if he was trying to find out how deep he could get it. Castiel took the incentive and sucked on the intruding muscle earning a delicious groan from Dean. Dean’s hands were still pressing against Castiel’s wrists but the grip became less firm and Castiel took the chance to push back a little moving away from the door slightly. Castiel continued to push in the direction of his double bed before Dean’s legs hit the mattress and Castiel just needed to give him one final push before he was sat on the bed with Castiel climbing into his lap and pressing their lips together once again. They parted for air and Dean was talking again as he panted “and here was me thinking that you wanted me to get your parents to like me”

“That was the plan” Castiel smiled as his hands roamed over the shirt Dean was wearing while Dean’s lips sucked at his neck. It fitted his chest so perfectly that Castiel couldn’t help but roam his hands over it feeling the toned muscle of Dean’s chest beneath the thin cotton. “But then I don’t give a fuck what they think because I love you and that’s all that matters” as soon as the words left his mouth, Castiel wished he could take them back. He knew he was in love with Dean and he was almost positive Dean loved him back but he also knew that Dean was afraid of his feelings and hardly ever talked about them. It was a miracle in itself that they had even been together for three months with Dean’s past record of a string of one night stands except for that one fling with Lisa he had been told about. Dean’s ministrations to his neck paused and Castiel was internally panicking that he had well and truly fucked up the best thing that had ever happened to him. “Dean-“ he began only to be cut off.

“I love you” Dean said staring him in the eyes.

It took half a second but as his heart pounded in his chest unable to control the feelings that were running through him at that moment his face broke into a wide grin as he saw relief stretch across Dean’s features before the smile that had started it all crossed his face.

In a swift movement, Castiel found himself being lifted and spun around so that he was lying on his back with Dean hovering over the top of him. Castiel wrapped his hand into Dean’s hair the other over the nape of his neck and pulled him down to press their lips together in a slow sensual kiss that expressed the words they had just spoken together. As their kisses continued, Castiel became aware of the prodding into his hip and couldn’t help but groan before he bucked his hips up seeking friction to his own hardened member. As Dean pushed back against him, it was then that he remembered that he was meant to be showing him his outfits although he really only wanted to show him one. Castiel’s hands slid to Dean’s shoulders and gently pushed him away so he could speak.

“Dean let me up so I can get changed” Castiel pleaded but Dean ignored him in favour of attacking his neck again. “Dean” he whined

“You look good as you are baby” Dean replied when he came up for air obviously forgetting what Castiel was planning to get changed into.

“No” Castiel said a little more forcefully and pushed Dean back so that he could look him in the eyes “Let me get changed” he said with a wiggle of his eyebrows. Confusion riddled across Dean’s features for a fraction of a second before realisation dawned on him and he pulled back eagerly with a smirk on his face. Castiel giggled as he pushed himself up and shuffled off the bed. When Dean slapped his rear, he let out yelp before turning around and grinning as he spoke “You’re going to pay for that”. Quickly, Castiel stepped into his wardrobe and closed the door firmly behind him. He walked down to the back where he had all his outfits hidden and other than when he wore the occasional one out when he was with friends or with Dean, most of them hadn’t left the walls of his room. He didn’t know how his parents would react to him liking to wear woman’s clothes but he didn’t think it would be a good reaction.

He explored his rack of clothes until he found the exact one he was looking for and hung it over the top of the mirror while he found the rest of the clothes he needed. He found his favourite blue panties and his black stilettoes and brought them over to the mirror and placed them on the floor while he stripped himself of his clothes. He strew them uncaringly across the floor eager to put his clothes on and to not leave Dean waiting too long. Once down to his birthday suit he slipped into his panties shivering at the feel of the silk on his skin before he settled them on his hips. He bit down on his lower lip as he caught a glance of himself in the mirror his erection prominent in the small garment. Satisfied that he looked pretty, he picked up the navy blue dress and stepped into it and brought it up over his shoulders. He zipped it up and then reached for the black belt which he fitted around his waist. He giggled as he heard the sound of metal dangling from the belt as he buckled it around him in anticipation of what he was going to do with Dean. When he was happy with how it sat on him, he stepped into his stilettoes and took a deep breath to calm himself. Normally he would do his make-up as well but as Dean was waiting for him and it would take him a while before he was happy with his make-up he didn’t want to waste any time. Instead, he walked confidently to the door and opened it before stepping through into his bedroom. Dean was sat on the bed with his feet on the floor facing the door Castiel was stood in with his jaw slack and his eyes wide.

“Fuck” he breathed as Castiel took a step closer to him. “Baby you look fucking gorgeous” Castiel blushed at Dean’s praise as he moved closer towards him until Dean could reach out and touch him. Hands settled on his hips dragging him even closer to his boyfriend until he was pulled into Dean’s lap so Dean could kiss him. “Do you have any idea how gorgeous you are baby?”

“Mmm I have an idea” Castiel smirked as he pushed Dean’s shoulders so he was laid back on the soft comforter. Castiel lifted himself to his knees so Dean could scoot back and lie more comfortably on the bed. “Now are you going to listen to me or am I going to have to use these?” Castiel reached to his belt and pulled out the metal cuffs that were tucked into it. He smirked as Dean’s eyes widened and his pupils blew wide with lust. Castiel didn’t even have to ask before Dean’s hands moved to the slated headboard and gripped tight. Castiel was surprised Dean wasn’t protesting against Castiel taking control like this but he wasn’t about to complain as he moved forward to lock Dean’s hands in place. When Dean confirmed for the fifth time that they weren’t too tight, Castiel pushed back and sat himself on Dean’s thighs.

While Castiel was getting changed, Dean had removed his tie so unbuttoning his boyfriend’s shirt was rather easy. His lips trailed down Dean’s chest as he popped open each button trailing lower and lower until his navel was revealed. Castiel kissed and sucked at Dean’s midway before smirking as he felt Dean’s arousal bump against his chin. His boyfriend was panting above him close to begging Castiel for more but Dean had more self-control than him so instead of waiting until Dean was actually begging him, Castiel open Dean’s slacks and tapped Dean’s hips in indication to lift them. Dean did so willingly and the younger teen pulled down both Dean’s slacks and briefs in one smooth movement. When they were pooled round his ankles, Castiel sat back down on Dean’s thighs.

“I have a surprise for you” he whispered before he turned around and lifted his ass into the air enough to show Dean his panties. He heard the groan that Dean let out and couldn’t stop the giggle that came out. “That’s not what I’m talking about” he teased before he raised one hand to his ass and pushed the fabric to the side to show a plastic plug in his ass.

“Fuck” Dean groaned “You had that in all through dinner?”

“Mhmm” Castiel answered before reaching up to grab the end of the plug and slowly pulled it out. He winced as it slipped out of him as his hole clenched around the emptiness but when he heard Dean moan in appreciation, he forgot about it all and shuffled back against Dean’s thighs before turning himself again. He raised himself to his knees and slid forward so he was hovering over Dean’s hard member but instead of lowering himself, he reached over to the bedside set of drawers to find the lube he had inside the top drawer. With the tube in hand, he popped the cap and squirted a decent amount onto his palm before shifting back and grasping Dean’s member. He threw the bottle of lube away as he focussed on slicking Dean up. Dean gasped loudly as Castiel’s hand enclosed around him and ever so slowly moved up and down making him nice a slick.

“Cas, please” Dean begged and Castiel couldn’t hold back much longer. He picked up the pace making sure Dean was adequately lubricated before he shuffled forward once again and raised himself over Dean’s cock. As he slowly sunk down, they groaned in unison. Castiel panted as he moved lower and lower as even though the plug was decently sized, it was not nearly as thick as Dean and the stretch burned a little as he moved. Once seated however, he panted as he adjusted before he leant forward and claimed Dean’s lips in a heated kiss. He could tell Dean was itching to thrust his hips up and to fuck him but he was being considerate and letting Castiel decide the movement. The kiss had distracted him enough from the burn and to test it out, the younger teen rocked his hips slightly. Dean moaned into his mouth as Castiel rolled more enthusiastically which had Castiel smirking before sliding his hands down Dean’s chest and pushing himself up. He dug his nails into his boyfriend’s pectorals as he moved his hips at a faster pace feeling every inch of Dean inside him.

When the teasing became too much, Castiel lifted himself up before slamming down again earning another delicious moan from Dean. He continued to rise and fall his nails leaving scratches on Dean’s torso and he hung on before he slipped his hands up Dean’s arms so he could link their hands together. He locked his fingers with Dean’s as he opened his eyes unaware he had closed them and stared into the older boy’s green eyes.

“Come on baby,” Dean panted “Ride me” Castiel’s hands squeezed Dean’s tighter as he picked up the pace lifting and falling groaning each time Dean’s dick brushed past his sweet spot. “So fucking beautiful baby” Dean continued as his thighs were burning but with the pleasure building in his gut, he had no desires to stop until Dean started to meet him thrust for thrust. “Come on Cas” he spurred “Fuck yourself on my dick I want to see you come” Castiel growled at the taunts which earned a smirk from the older teen before he was moving with abandon impaling his body hard. He knew Dean was close from the way his hips would stutter and his head was thrown back into the pillows and he was determined to get Dean there first. His muscles protested but he was moving as fast as he could until Dean was crying out Castiel’s name and coming inside him. Castiel rode him through it before he stilled his movements as Dean came down from his high until he was sure he was finished.

Slowly, Castiel rose himself up clenching down trying to keep all of Dean’s come inside him. Dean let out a squeak of protest and the sensation but the younger teen ignored it in favour of shuffling forward trying not to let any come leak out of him.

“I want to ride your face now” Castiel panted as he smiled down at Dean. Dean looked at him as if he was all for the idea and desperate to have Castiel sit on his face so Castiel inched forward more before rising up onto his heels so he was squatting over Dean’s chest. He sat down on his boyfriend’s torso and pulled is feet up so they were hooked under Dean’s arms which were still handcuffed to the bed. Castiel reached his hand out to grab hold of the headboard to balance him as he pulled himself up and hovered over Dean’s face. He looked down his body to see Dean’s eyes hungry for him and it made his dick twitch to see his boyfriend so hungry to eat him out. Castiel let himself sink slowly until he felt the touch of Dean’s wet tongue to his fucked out hole making him gasp. “Fuck” he groaned as Dean’s tongue worked over the well-used muscle before delving inside. His hips started to rock once again riding Dean’s tongue as it worked inside of him licking and sucking the semen from inside him. “God your tongue” Castiel keened as he continued to rock gripping the headboard impossibly tighter as he felt the familiar feeling pool deep in his gut once again.

“ _Dean, Dean, Dean_ ” he chanted as his hips drove wildly wanting more of Dean’s tongue inside his ass. His cock was hard and leaking all over his panties and his dress as he drove closer and closer to his orgasm. “God Dean more please” he sobbed as Dean moaned into his ass sending vibrations through him driving him absolutely crazy. Dean’s head lifted off the mattress to get more inside of Castiel his nose brushing the sensitive skin behind his balls causing more curses and cries of ‘Dean’ to be shuddered from Castiel’s lips before it was all over and Castiel was coming all over himself. Dean’s tongue worked him through it and although he had ruined his dress, he failed to care as he shifted back and sat on Dean’s chest once again. He collapsed down sealing their mouths together delving his tongue inside so he could taste himself mixed with Dean from his boyfriend’s mouth. Breathless he pulled away before settling down on Dean’s chest tucking his head under his boyfriend’s chin.

After a few moments of silence, Dean broke it “Hey Cas, mind taking these things off?” Castiel raised his head completely forgetting that Dean was still attached to the headboard. With the last bit of energy his body possessed, Castiel reached down to his belt where he knew the keys were kept and pulled them out before uncuffing Dean and collapsing back down exhausted. Hands pushed through his hair and down his back rubbing soothingly and Castiel sighed as he snuggled deeper into Dean’s sweaty chest. “You were so fucking awesome baby. I don’t even care if your parents heard us because you are fucking beautiful. So perfect for me” Castiel chuckled weakly as he fought off the urge to sleep. He pressed a lazy kiss into Dean’s heated skin as he felt his eyelids droop. “Go to sleep babe. You can show me the rest of your wardrobe after some rest” Castiel nodded before he let himself succumb to sleep as the excitement of the day wore off. He loved Dean and Dean loved him even if his parents hated Dean especially if they had heard the ruckus they had worked up he didn’t care because he had Dean and that was all that mattered. 

**Notes for the Chapter:**

> My [tumblr](http://www.assbuttintheimpalafiction.tumblr.com) for those who want to follow me there


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